Senior Strategic Account Manager, Gladly
Upper Enterprise
+ Stock options
Customer experience AI built for LTV
Be an early applicant
Customer experience AI built for LTV
201-500 employees
Be an early applicant
+ Stock options
201-500 employees
Company mission
To make customer service radically personal.
Role
Who you are
- The ideal candidate has a track record of growing strategic customer accounts
- You are someone who can command a room with C-suite stakeholders, relentlessly identify white space business opportunities, and translate Gladly’s Customer AI capabilities into revenue-generating outcomes for both the customer and Gladly
- You are an expert at building trusted relationships, internally as a cross-functional leader and externally across various levels of an organization, that enable you to drive performance and great win-win outcomes
- Experience: 8+ years in a quota-carrying, client-facing role (Strategic Account Management, Install Base Sales, or Expansion Sales) within a SaaS environment. Enterprise high-touch experience is required
- Revenue Track Record: Demonstrated success exceeding net retention plus expansion targets, including six-to-seven figure renewals and commercial negotiations
- Portfolio Management: Strong ability to lead and manage through higher-volume Book of Business periods without sacrificing quality of engagement or commercial rigor
- Ownership & Initiative: A proactive, “CEO of your book” mindset. You don’t wait for direction. You anticipate customer needs, identify risk, and drive action independently
- Executive Presence: The ability to hold your own with C-suite stakeholders (think: VP of CX at a Fortune 500 retailer). You command a room, not just present in one
- Commercial Mindset: A relentless focus on growing revenue. You see every customer interaction as an opportunity to identify white space and drive commercial outcomes
- Customer Obsession: You care deeply about your customers, helping them achieve their goals, and making them raving fans of Gladly in the process. Customer devotion and commercial performance aren’t at odds, they fuel each other
- Strategic Thinking: Proven ability to build multi-threaded account strategies, navigate complex organizational hierarchies, and create actionable roadmaps tied to impact
- Underdog Grit: A willingness to learn, adapt, and strive for excellence in an environment that values transparency and winning as one team
- If this role excites you but you don't meet every qualification, we still encourage you to apply. The perspectives and experiences you bring matter more than checking every box
What the job involves
- You will join a high-impact team of strategic account managers who own revenue outcomes across our most valuable Enterprise accounts. We don’t just manage accounts; we operate as the CEO of our book of business—driving net dollar retention, identifying expansion opportunities, and delivering measurable ROI for B2C leaders
- We are looking for a Senior Strategic Account Manager to own a portfolio of 7–10 high-touch Upper Enterprise accounts. This is a revenue-accountable role where you will be the single owner of your book; responsible for renewals, expansion, and net dollar retention
- Revenue Ownership: Carry a net dollar retention target across your portfolio. Own the full renewal cycle, drive cross-sell revenue through increasing AI product adoption, and proactively identify and close upsell revenue
- Strategic Account Planning: Build and execute comprehensive account plans that map white space, identify key stakeholders, and align Gladly’s platform with each customer’s strategic priorities and business outcomes
- Executive Engagement: Own all executive-level relationships and engagement. Lead Customer QBRs and EBRs independently,translating platform data into business outcomes that resonate with executive stakeholders ranging from CIOs, CTOs, CDOs, and COOs to VPs of CX (Support, Service, etc.), VPs of IT, and beyond
- Commercial Negotiation: Lead complex, multi-stakeholder renewal and expansion negotiations. Navigate procurement, legal, and executive approval processes with confidence and urgency
- Product & Solutions Expertise: Leverage deep knowledge of Gladly’s platform and Customer AI capabilities to recommend solutions that drive radical efficiency and customer devotion. Position Gladly’s AI products as strategic investments, not line items
- Cross-functional Leadership: Partner closely with Sales, Product, and CX teams to ensure the Voice of the Customer shapes our roadmap. Hold internal and external stakeholders accountable to timelines and commitments
Our take
Gladly is a cloud-based platform integrating multiple customer service channels into a single UI. It helps companies cater to the upward trend in personalized service by allowing them to communicate with their customers seamlessly across any channel from voice, email, messaging, chat and social media.
The rise in eCommerce has meant demand for services like Gladly is growing. To stand out, the company has focussed on building out its platform with new features. Most lately, this has included an AI and automation-driven customer service platform.
As a certified app partner to Shopify, Gladly benefits from the ability of Shopify merchants to integrate directly with its platform. The company has raised considerable funding, the latest of which supports accelerated growth on the back of releasing its unified customer service platform.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
15% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Sep 2024
$40m
LATE VC
Dec 2022
$55m
LATE VC
Total funding: $208m
Company benefits
- Stock options
- Medical, Dental, Vision and Life insurance
- Generous paid time off
- Generous paid Parental Leave
- 401K
- Flexible Spending Accounts
- Home office stipends
Company HQ
Bernal Heights, San Francisco, CA
Leadership
Charlie Besecker
(CEO)Charlie joined Gladly in 2024 as a President, moving into the role of CEO in 2025. Prior to this, he was a CRO at GRIN and Route.
Joseph Ansanelli
(Co-Founder & Executive Chairman)After co-founding Gladly in 2015, Joseph served as the CEO until 2025. He has also been at Greylock since 2012, spending 5 years as a General Partner before becoming a Venture Partner.
Andy D'Amato
(CRO)Prior to joining Gladly in 2022, Andy spent nearly 9 years at PTC. While there he held a number of roles, including Senior VP of Sales, Americas IoT & Augmented Reality and Senior VP of Global IoT Sales.
Todd Rakow
(CFO)Todd joined Gladly in 2019 as a VP of FInance & Operations before moving into the role of CFO in 2022. Previously, he co-founded Kanjoya and served as the CFO for nearly 6 years. He also spent some time at PayPal as a Senior Operations & Strategy Manager.
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